Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic apparatus

Abstract

A compound represented by the following formula (1).

Description

TECHNICAL FIELD

[0001] The present invention relates to a novel compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic apparatus.BACKGROUND ART

[0002] When voltage is applied to an organic electroluminescence device (hereinafter, also referred to as an organic EL device), holes and electrons are injected into an emitting layer from an anode and a cathode, respectively. Then, thus injected holes and electrons are recombined in the emitting layer, and excitons are formed therein.

[0003] Conventional organic EL devices have not yet had sufficient device performance. Although materials used for the organic EL device are gradually improved to enhance the device performance, further performance enhancement is required.SUMMARY OF THE INVENTION

[0004] It is an object of the present invention to provide an organic EL device having high performance, and a compound capable of achieving the organic EL device.

[0005] As a result of intensive studies to achieve the above object, the present inventors have found that an organic EL device having high performance can be obtained by using a compound having the specific structure, and have completed the present invention.

[0006] According to the present invention, the following compound and the like are provided.

[0007] 1. A compound represented by the following formula (1):wherein in the formula (1),

[0009] X1 and X2 are independently N or CH; any one of X1 and X2 is N;

[0010] Ar1 and Ar2 are independently

[0011] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0012] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

[0013] L1 to L3 are independently

[0014] a single bond,

[0015] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0016] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

[0017] n1 is integer 0 to 4; when n1 is 0, (L1)n1 is single bond; when a plurality of L1's is present, the plurality of L1's may be the same as or different from each other;

[0018] n2 is integer 0 to 4; when n2 is 0, (L2)n2 is single bond; when a plurality of L2's is present, the plurality of L2's may be the same as or different from each other;

[0019] n3 is integer 0 to 4; when n3 is 0, (L3)n3 is single bond; when a plurality of L3's is present, the plurality of L3's may be the same as or different from each other;

[0020] R11 to R19 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R11 to R19 does not bond with each other;

[0021] R21 and R22 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form the substituted or unsubstituted, saturated or unsaturated ring;

[0022] R21 and R22 which do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

[0023] a hydrogen atom,

[0024] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[0025] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

[0026] the substituent R is selected from the group consisting of

[0027] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0028] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0029] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0030] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0031] —Si(R901)(R902)(R903),

[0032] —O—(R904),

[0033] S—(R905),

[0034] —N(R906)(R907),

[0035] a halogen atom, a cyano group, a nitro group,

[0036] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0037] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

[0038] R901 to R907 are independently

[0039] a hydrogen atom,

[0040] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0041] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0042] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0043] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

[0044] when two or more of each of R901 to R907 are present, the two or more of each of R901 to R907 may be the same as or different from each other; and

[0045] when two or more substituents R are present, the two or more substituents R may be the same as or different from each other.

[0046] 2. An organic electroluminescence device comprising

[0047] a cathode,

[0048] an anode, and

[0049] one or two or more organic layers arranged between the cathode and the anode,

[0050] wherein at least one layer of the organic layers comprises the compound according to 1.

[0051] 3. An electronic apparatus comprising the organic electroluminescence device according to 2.

[0052] According to the present invention, there can be provided an organic EL device having high performance, and a compound capable of achieving the organic EL device.BRIEF DESCRIPTION OF THE DRAWINGS

[0053] FIG. 1 is a diagram showing a schematic configuration of an organic EL device according to an aspect of the present invention.MODE FOR CARRYING OUT THE INVENTIONDefinition

[0054] In this specification, a hydrogen atom includes its isotopes different in the number of neutrons, namely, a protium, a deuterium and a tritium.

[0055] In this specification, at a bondable position in a chemical formula where a symbol such as “R”, or “D” representing a deuterium atom is not indicated, a hydrogen atom, that is, a protium atom, a deuterium atom or a tritium atom is bonded.

[0056] In this specification, the number of ring carbon atoms represents the number of carbon atoms forming a subject ring itself among the carbon atoms of a compound having a structure in which atoms are bonded in a ring form (for example, a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound). When the subject ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The same shall apply to “the number of ring carbon atoms” described below, unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring includes 10 ring carbon atoms, a pyridine ring includes 5 ring carbon atoms, and a furan ring includes 4 ring carbon atoms. Further, for example, a 9,9-diphenylfluorenyl group includes 13 ring carbon atoms, and a 9,9′-spirobifluorenyl group includes 25 ring carbon atoms.

[0057] When a benzene ring is substituted by, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the benzene ring. Therefore, the number of ring carbon atoms of the benzene ring substituted by the alkyl group is 6. When a naphthalene ring is substituted by, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms of the naphthalene ring. Therefore, the number of ring carbon atoms of the naphthalene ring substituted by the alkyl group is 10.

[0058] In this specification, the number of ring atoms represents the number of atoms forming a subject ring itself among the atoms of a compound having a structure in which atoms are bonded in a ring form (for example, the structure includes a monocyclic ring, a fused ring and a ring assembly) (for example, a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound and a heterocyclic compound). The number of ring atoms does not include atoms which do not form the ring (for example, a hydrogen atom which terminates a bond of the atoms forming the ring), or atoms contained in a substituent when the ring is substituted by the substituent. The same shall apply to “the number of ring atoms” described below, unless otherwise specified. For example, the number of atoms of a pyridine ring is 6, the number of atoms of a quinazoline ring is 10, and the number of a furan ring is 5. For example, hydrogen atoms bonded to a pyridine ring and atoms constituting a substituent substituted on the pyridine ring are not included in the number of ring atoms of the pyridine ring. Therefore, the number of ring atoms of a pyridine ring with which a hydrogen atom or a substituent is bonded is 6. For example, hydrogen atoms and atoms constituting a substituent which are bonded with a quinazoline ring is not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of a quinazoline ring with which a hydrogen atom or a substituent is bonded is 10.

[0059] In this specification, “XX to YY carbon atoms” in the expression “a substituted or unsubstituted ZZ group including XX to YY carbon atoms” represents the number of carbon atoms in the case where the ZZ group is unsubstituted by a substituent, and does not include the number of carbon atoms of a substituent in the case where the ZZ group is substituted by the substituent. Here, “YY” is larger than “XX”, and “XX” means an integer of 1 or more and “YY” means an integer of 2 or more.

[0060] In this specification, “XX to YY atoms” in the expression “a substituted or unsubstituted ZZ group including XX to YY atoms” represents the number of atoms in the case where the ZZ group is unsubstituted by a substituent, and does not include the number of atoms of a substituent in the case where the ZZ group is substituted by the substituent. Here, “YY” is larger than “XX”, and “XX” means an integer of 1 or more and “YY” means an integer of 2 or more.

[0061] In this specification, the unsubstituted ZZ group represents the case where the “substituted or unsubstituted ZZ group” is a “ZZ group unsubstituted by a substituent”, and the substituted ZZ group represents the case where the “substituted or unsubstituted ZZ group” is a “ZZ group substituted by a substituent”.

[0062] In this specification, a term “unsubstituted” in the case of “a substituted or unsubstituted ZZ group” means that hydrogen atoms in the ZZ group are not substituted by a substituent. Hydrogen atoms in a term “unsubstituted ZZ group” are a protium atom, a deuterium atom, or a tritium atom.

[0063] In this specification, a term “substituted” in the case of “a substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group are substituted by a substituent. Similarly, a term “substituted” in the case of “a BB group substituted by an AA group” means that one or more hydrogen atoms in the BB group are substituted by the AA group.“Substituent as Described in this Specification”

[0064] Hereinafter, the substituent described in this specification will be explained.

[0065] The number of ring carbon atoms of the “unsubstituted aryl group” described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified.

[0066] The number of ring atoms of the “unsubstituted heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified.

[0067] The number of carbon atoms of the “unsubstituted alkyl group” described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified.

[0068] The number of carbon atoms of the “unsubstituted alkenyl group” described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified.

[0069] The number of carbon atoms of the “unsubstituted alkynyl group” described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified.

[0070] The number of ring carbon atoms of the “unsubstituted cycloalkyl group” described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified.

[0071] The number of ring carbon atoms of the “unsubstituted arylene group” described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified.

[0072] The number of ring atoms of the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified.

[0073] The number of carbon atoms of the “unsubstituted alkylene group” described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified.“Substituted or Unsubstituted Aryl Group”

[0074] Specific examples of the “substituted or unsubstituted aryl group” described in this specification (specific example group G1) include the following unsubstituted aryl groups (specific example group G1A), substituted aryl groups (specific example group GIB), and the like. (Here, the unsubstituted aryl group refers to the case where the “substituted or unsubstituted aryl group” is an “aryl group unsubstituted by a substituent”, and the substituted aryl group refers to the case where the “substituted or unsubstituted aryl group” is an “aryl group substituted by a substituent”.). In this specification, in the case where simply referred as an “aryl group”, it includes both a “unsubstituted aryl group” and a “substituted aryl group.”

[0075] The “substituted aryl group” means a group in which one or more hydrogen atoms of the “unsubstituted aryl group” are substituted by a substituent. Specific examples of the “substituted aryl group” include, for example, groups in which one or more hydrogen atoms of the “unsubstituted aryl group” of the following specific example group G1A are substituted by a substituent, the substituted aryl groups of the following specific example group G1B, and the like. It should be noted that the examples of the “unsubstituted aryl group” and the examples of the “substituted aryl group” enumerated in this specification are mere examples, and the “substituted aryl group” described in this specification also includes a group in which a hydrogen atom bonded with a carbon atom of the aryl group itself in the “substituted aryl group” of the following specific group G1B is further substituted by a substituent, and a group in which a hydrogen atom of a substituent in the “substituted aryl group” of the following specific group G1B is further substituted by a substituent.Unsubstituted Aryl Group (Specific Example Group G1A):a phenyl group,

[0077] a p-biphenyl group,

[0078] a m-biphenyl group,

[0079] an o-biphenyl group,

[0080] a p-terphenyl-4-yl group,

[0081] a p-terphenyl-3-yl group,

[0082] a p-terphenyl-2-yl group,

[0083] a m-terphenyl-4-yl group,

[0084] a m-terphenyl-3-yl group,

[0085] a m-terphenyl-2-yl group,

[0086] an o-terphenyl-4-yl group,

[0087] an o-terphenyl-3-yl group,

[0088] an o-terphenyl-2-yl group,

[0089] a 1-naphthyl group,

[0090] a 2-naphthyl group,

[0091] an anthryl group,

[0092] a benzanthryl group,

[0093] a phenanthryl group,

[0094] a benzophenanthryl group,

[0095] a phenalenyl group,

[0096] a pyrenyl group,

[0097] a chrysenyl group,

[0098] a benzochrysenyl group,

[0099] a triphenylenyl group,

[0100] a benzotriphenylenyl group,

[0101] a tetracenyl group,

[0102] a pentacenyl group,

[0103] a fluorenyl group,

[0104] a 9,9′-spirobifluorenyl group,

[0105] a benzofluorenyl group,

[0106] a dibenzofluorenyl group,

[0107] a fluoranthenyl group,

[0108] a benzofluoranthenyl group,

[0109] a perylenyl group, and

[0110] a monovalent aryl group derived by removing one hydrogen atom from the ring structures represented by each of the following general formulas (TEMP-1) to (TEMP-15).Substituted Aryl Group (Specific Example Group G1B):an o-tolyl group,a m-tolyl group,

[0113] a p-tolyl group,

[0114] a p-xylyl group,

[0115] a m-xylyl group,

[0116] an o-xylyl group,

[0117] a p-isopropylphenyl group,

[0118] a m-isopropylphenyl group,

[0119] an o-isopropylphenyl group,

[0120] a p-t-butylphenyl group,

[0121] a m-t-butylphenyl group,

[0122] an o-t-butylphenyl group,

[0123] a 3,4,5-trimethylphenyl group,

[0124] a 9,9-dimethylfluorenyl group,

[0125] a 9,9-diphenylfluorenyl group,

[0126] a 9,9-bis(4-methylphenyl)fluorenyl group,

[0127] a 9,9-bis(4-isopropylphenyl)fluorenyl group,

[0128] a 9,9-bis(4-t-butylphenyl)fluorenyl group,

[0129] a cyanophenyl group,

[0130] a triphenylsilylphenyl group,

[0131] a trimethylsilylphenyl group,

[0132] a phenylnaphthyl group,

[0133] a naphthylphenyl group, and

[0134] a group in which one or more hydrogen atoms of a monovalent group derived from the ring structures represented by each of the general formulas (TEMP-1) to (TEMP-15) are substituted by a substituent.“Substituted or Unsubstituted Heterocyclic Group”

[0135] The “heterocyclic group” described in this specification is a ring group having at least one hetero atom in the ring atom. Specific examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.

[0136] The “heterocyclic group” in this specification is a monocyclic group or a fused ring group.

[0137] The “heterocyclic group” in this specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0138] Specific examples of the “substituted or unsubstituted heterocyclic group” (specific example group G2) described in this specification include the following unsubstituted heterocyclic group (specific example group G2A), the following substituted heterocyclic group (specific example group G2B), and the like. (Here, the unsubstituted heterocyclic group refers to the case where the “substituted or unsubstituted heterocyclic group” is a “heterocyclic group unsubstituted by a substituent”, and the substituted heterocyclic group refers to the case where the “substituted or unsubstituted heterocyclic group” is a “heterocyclic group substituted by a substituent”.). In this specification, in the case where simply referred as a “heterocyclic group”, it includes both the “unsubstituted heterocyclic group” and the “substituted heterocyclic group.”

[0139] The “substituted heterocyclic group” means a group in which one or more hydrogen atom of the “unsubstituted heterocyclic group” are substituted by a substituent. Specific examples of the “substituted heterocyclic group” include a group in which a hydrogen atom of “unsubstituted heterocyclic group” of the following specific example group G2A is substituted by a substituent, the substituted heterocyclic groups of the following specific example group G2B, and the like. It should be noted that the examples of the “unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” enumerated in this specification are mere examples, and the “substituted heterocyclic group” described in this specification includes groups in which hydrogen atom bonded with a ring atom of the heterocyclic group itself in the “substituted heterocyclic group” of the specific example group G2B is further substituted by a substituent, and a group in which hydrogen atom of a substituent in the “substituted heterocyclic group” of the specific example group G2B is further substituted by a substituent.

[0140] Specific example group G2A includes, for example, the following unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1), the following unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2), the following unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3), and the monovalent heterocyclic group derived by removing one hydrogen atom from the ring structures represented by each of the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0141] Specific example group G2B includes, for example, the following substituted heterocyclic group containing a nitrogen atom (specific example group G2B1), the following substituted heterocyclic group containing an oxygen atom (specific example group G2B2), the following substituted heterocyclic group containing a sulfur atom (specific example group G2B3), and the following group in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structures represented by each of the following general formulas (TEMP-16) to (TEMP-33) are substituted by a substituent (specific example group G2B4).Unsubstituted Heterocyclic Group Containing a Nitrogen Atom (Specific Example Group G2A1):a pyrrolyl group,

[0143] an imidazolyl group,

[0144] a pyrazolyl group,

[0145] a triazolyl group,

[0146] a tetrazolyl group,

[0147] an oxazolyl group,

[0148] an isoxazolyl group,

[0149] an oxadiazolyl group,

[0150] a thiazolyl group,

[0151] an isothiazolyl group,

[0152] a thiadiazolyl group,

[0153] a pyridyl group,

[0154] a pyridazinyl group,

[0155] a pyrimidinyl group,

[0156] a pyrazinyl group,

[0157] a triazinyl group,

[0158] an indolyl group,

[0159] an isoindolyl group,

[0160] an indolizinyl group,

[0161] a quinolizinyl group,

[0162] a quinolyl group,

[0163] an isoquinolyl group,

[0164] a cinnolyl group,

[0165] a phthalazinyl group,

[0166] a quinazolinyl group,

[0167] a quinoxalinyl group,

[0168] a benzimidazolyl group,

[0169] an indazolyl group,

[0170] a phenanthrolinyl group,

[0171] a phenanthridinyl group,

[0172] an acridinyl group,

[0173] a phenazinyl group,

[0174] a carbazolyl group,

[0175] a benzocarbazolyl group,

[0176] a morpholino group,

[0177] a phenoxazinyl group,

[0178] a phenothiazinyl group,

[0179] an azacarbazolyl group, and

[0180] a diazacarbazolyl group.Unsubstituted Heterocyclic Group Containing an Oxygen Atom (Specific Example Group G2A2):a furyl group,

[0182] an oxazolyl group,

[0183] an isoxazolyl group,

[0184] an oxadiazolyl group,

[0185] a xanthenyl group,

[0186] a benzofuranyl group,

[0187] an isobenzofuranyl group,

[0188] a dibenzofuranyl group,

[0189] a naphthobenzofuranyl group,

[0190] a benzoxazolyl group,

[0191] a benzisoxazolyl group,

[0192] a phenoxazinyl group,

[0193] a morpholino group,

[0194] a dinaphthofuranyl group,

[0195] an azadibenzofuranyl group,

[0196] a diazadibenzofuranyl group,

[0197] an azanaphthobenzofuranyl group, and

[0198] a diazanaphthobenzofuranyl group.Unsubstituted Heterocyclic Group Containing a Sulfur Atom (Specific Example Group G2A3):a thienyl group,

[0200] a thiazolyl group,

[0201] an isothiazolyl group,

[0202] a thiadiazolyl group,

[0203] a benzothiophenyl group (benzothienyl group),

[0204] an isobenzothiophenyl group (isobenzothienyl group),

[0205] a dibenzothiophenyl group (dibenzothienyl group),

[0206] a naphthobenzothiophenyl group (naphthobenzothienyl group),

[0207] a benzothiazolyl group,

[0208] a benzisothiazolyl group,

[0209] a phenothiazinyl group,

[0210] a dinaphthothiophenyl group (dinaphthothienyl group),

[0211] an azadibenzothiophenyl group (azadibenzothienyl group),

[0212] a diazadibenzothiophenyl group (diazadibenzothienyl group),

[0213] an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and

[0214] a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).Monovalent Heterocyclic Group Derived by Removing One Hydrogen Atom from the Ring Structures Represented by Each of the Following General Formulas (TEMP-16) to (TEMP-33) (Specific Example Group G2A4):

[0215] In the general formulas (TEMP-16) to (TEMP-33), XA and YA are independently an oxygen atom, a sulfur atom, NH, or CH2. Provided that at least one of XA and YA is an oxygen atom, a sulfur atom, or NH.

[0216] In the general formulas (TEMP-16) to (TEMP-33), when at least one of XA and YA is NH or CH2, the monovalent heterocyclic group derived from the ring structures represented by each of the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group derived by removing one hydrogen atom from these NH or CH2.Substituted Heterocyclic Group Containing a Nitrogen Atom (Specific Example Group G2B1):a (9-phenyl)carbazolyl group,

[0218] a (9-biphenylyl)carbazolyl group,

[0219] a (9-phenyl)phenylcarbazolyl group,

[0220] a (9-naphthyl)carbazolyl group,

[0221] a diphenylcarbazol-9-yl group,

[0222] a phenylcarbazol-9-yl group,

[0223] a methylbenzimidazolyl group,

[0224] an ethylbenzimidazolyl group,

[0225] a phenyltriazinyl group,

[0226] a biphenylyltriazinyl group,

[0227] a diphenyltriazinyl group,

[0228] a phenylquinazolinyl group, and

[0229] a biphenylylquinazolinyl group.Substituted Heterocyclic Group Containing an Oxygen Atom (Specific Example Group G2B2):a phenyldibenzofuranyl group,

[0231] a methyldibenzofuranyl group,

[0232] a t-butyldibenzofuranyl group, and

[0233] a monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].Substituted Heterocyclic Group Containing a Sulfur Atom (Specific Example Group G2B3):a phenyldibenzothiophenyl group,

[0235] a methyldibenzothiophenyl group,

[0236] a t-butyldibenzothiophenyl group, and

[0237] a monovalent residue of spiro[9H-thioxanthene-9,9′-[9H]fluorene].Group in which One or More Hydrogen Atoms of the Monovalent Heterocyclic Group Derived from the Ring Structures Represented by Each of the Following General Formulas (TEMP-16) to (TEMP-33) are Substituted by a Substituent (Specific Example Group G2B4):

[0238] The “one or more hydrogen atoms of the monovalent heterocyclic group” means one or more hydrogen atoms selected from hydrogen atoms bonded with ring carbon atoms of the monovalent heterocyclic group, a hydrogen atom bonded with a nitrogen atom when at least one of XA and YA is NH, and hydrogen atoms of a methylene group when one of XA and YA is CH2.“Substituted or Unsubstituted Alkyl Group”

[0239] Specific examples of the “substituted or unsubstituted alkyl group” (specific example group G3) described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and the following substituted alkyl groups (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the “substituted or unsubstituted alkyl group” is an “alkyl group unsubstituted by a substituent”, and the substituted alkyl group refers to the case where the “substituted or unsubstituted alkyl group” is an “alkyl group substituted by a substituent”.). In this specification, in the case where simply referred as an “alkyl group” includes both the “unsubstituted alkyl group” and the “substituted alkyl group.”

[0240] The “substituted alkyl group” means a group in which one or more hydrogen atoms in the “unsubstituted alkyl group” are substituted by a substituent. Specific examples of the “substituted alkyl group” include groups in which one or more hydrogen atoms in the following “unsubstituted alkyl group” (specific example group G3A) are substituted by a substituent, the following substituted alkyl group (specific example group G3B), and the like. In this specification, the alkyl group in the “unsubstituted alkyl group” means a linear alkyl group. Thus, the “unsubstituted alkyl group” includes a straight-chain “unsubstituted alkyl group” and a branched-chain “unsubstituted alkyl group”. It should be noted that the examples of the “unsubstituted alkyl group” and the examples of the “substituted alkyl group” enumerated in this specification are mere examples, and the “substituted alkyl group” described in this specification includes a group in which hydrogen atom of the alkyl group itself in the “substituted alkyl group” of the specific example group G3B is further substituted by a substituent, and a group in which hydrogen atom of a substituent in the “substituted alkyl group” of the specific example group G3B is further substituted by a substituent.Unsubstituted Alkyl Group (Specific Example Group G3A):a methyl group,

[0242] an ethyl group,

[0243] a n-propyl group,

[0244] an isopropyl group,

[0245] a n-butyl group,

[0246] an isobutyl group,

[0247] a s-butyl group, and

[0248] a t-butyl group.Substituted Alkyl Group (Specific Example Group G3B):a heptafluoropropyl group (including isomers),

[0250] a pentafluoroethyl group,

[0251] a 2,2,2-trifluoroethyl group, and

[0252] a trifluoromethyl group.“Substituted or Unsubstituted Alkenyl Group”

[0253] Specific examples of the “substituted or unsubstituted alkenyl group” described in this specification (specific example group G4) include the following unsubstituted alkenyl group (specific example group G4A), the following substituted alkenyl group (specific example group G4B), and the like. (Here, the unsubstituted alkenyl group refers to the case where the “substituted or unsubstituted alkenyl group” is a “alkenyl group unsubstituted by a substituent”, and the “substituted alkenyl group” refers to the case where the “substituted or unsubstituted alkenyl group” is a “alkenyl group substituted by a substituent.”). In this specification, in the case where simply referred as an “alkenyl group” includes both the “unsubstituted alkenyl group” and the “substituted alkenyl group.”

[0254] The “substituted alkenyl group” means a group in which one or more hydrogen atoms in the “unsubstituted alkenyl group” are substituted by a substituent. Specific examples of the “substituted alkenyl group” include a group in which the following “unsubstituted alkenyl group” (specific example group G4A) has a substituent, the following substituted alkenyl group (specific example group G4B), and the like. It should be noted that the examples of the “unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” enumerated in this specification are mere examples, and the “substituted alkenyl group” described in this specification includes a group in which a hydrogen atom of the alkenyl group itself in the “substituted alkenyl group” of the specific example group G4B is further substituted by a substituent, and a group in which a hydrogen atom of a substituent in the “substituted alkenyl group” of the specific example group G4B is further substituted by a substituent.Unsubstituted Alkenyl Group (Specific Example Group G4A):a vinyl group,

[0256] an allyl group,

[0257] a 1-butenyl group,

[0258] a 2-butenyl group, and

[0259] a 3-butenyl group.Substituted Alkenyl Group (Specific Example Group G4B):a 1,3-butanedienyl group,

[0261] a 1-methylvinyl group,

[0262] a 1-methylallyl group,

[0263] a 1,1-dimethylallyl group,

[0264] a 2-methylally group, and

[0265] a 1,2-dimethylallyl group.“Substituted or Unsubstituted Alkynyl Group”

[0266] Specific examples of the “substituted or unsubstituted alkynyl group” described in this specification (specific example group G5) include the following unsubstituted alkynyl group (specific example group G5A) and the like. (Here, the unsubstituted alkynyl group refers to the case where the “substituted or unsubstituted alkynyl group” is an “alkynyl group unsubstituted by a substituent”.). In this specification, in the case where simply referred as an “alkynyl group” includes both the “unsubstituted alkynyl group” and the “substituted alkynyl group.”

[0267] The “substituted alkynyl group” means a group in which one or more hydrogen atoms in the “unsubstituted alkynyl group” are substituted by a substituent. Specific examples of the “substituted alkynyl group” include a group in which one or more hydrogen atoms in the following “unsubstituted alkynyl group” (specific example group G5A) are substituted by a substituent, and the like.Unsubstituted Alkynyl Group (Specific Example Group G5A):an ethynyl group.“Substituted or Unsubstituted Cycloalkyl Group”

[0269] Specific examples of the “substituted or unsubstituted cycloalkyl group” described in this specification (specific example group G6) include the following unsubstituted cycloalkyl group (specific example group G6A), the following substituted cycloalkyl group (specific example group G6B), and the like. (Here, the unsubstituted cycloalkyl group refers to the case where the “substituted or unsubstituted cycloalkyl group” is a “cycloalkyl group unsubstituted by a substituent”, and the substituted cycloalkyl group refers to the case where the “substituted or unsubstituted cycloalkyl group” is a “cycloalkyl group substituted by a substituent”.). In this specification, in the case where simply referred as a “cycloalkyl group” includes both the “unsubstituted cycloalkyl group” and the “substituted cycloalkyl group.”

[0270] The “substituted cycloalkyl group” means a group in which one or more hydrogen atoms in the “unsubstituted cycloalkyl group” are substituted by a substituent. Specific examples of the “substituted cycloalkyl group” include a group in which one or more hydrogen atoms in the following “unsubstituted cycloalkyl group” (specific example group G6A) are substituted by a substituent, and examples of the following substituted cycloalkyl group (specific example group G6B), and the like. It should be noted that the examples of the “unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” enumerated in this specification are mere examples, and the “substituted cycloalkyl group” in this specification includes a group in which one or more hydrogen atoms bonded with the carbon atom of the cycloalkyl group itself in the “substituted cycloalkyl group” of the specific example group G6B are substituted by a substituent, and a group in which a hydrogen atom of a substituent in the “substituted cycloalkyl group” of specific example group G6B is further substituted by a substituent.Unsubstituted Cycloalkyl Group (Specific Example Group G6A):a cyclopropyl group,

[0272] a cyclobutyl group,

[0273] a cyclopentyl group,

[0274] a cyclohexyl group,

[0275] a 1-adamantyl group,

[0276] a 2-adamantyl group,

[0277] a 1-norbornyl group, and

[0278] a 2-norbornyl group.Substituted Cycloalkyl Group (Specific Example Group G6B):a 4-methylcyclohexyl group.“Group Represented by —Si(R901)(R902)(R903)”

[0280] Specific examples of the group represented by —Si(R901)(R902)(R903) described in this specification (specific example group G7) include:

[0281] —Si(G1)(G1)(G1),

[0282] —Si(G1)(G2)(G2),

[0283] —Si(G1)(G1)(G2),

[0284] —Si(G2)(G2)(G2),

[0285] —Si(G3)(G3)(G3), and

[0286] —Si(G6)(G6)(G6).

[0287] G1 is the “substituted or unsubstituted aryl group” described in the specific example group G1.

[0288] G2 is the “substituted or unsubstituted heterocyclic group” described in the specific example group G2.

[0289] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0290] G6 is the “substituted or unsubstituted cycloalkyl group” described in the specific example group G6.

[0291] Plural G1's in —Si(G1)(G1)(G1) are the same or different.

[0292] Plural G2's in —Si(G1)(G2)(G2) are the same or different.

[0293] Plural G1's in —Si(G1)(G1)(G2) are the same or different.

[0294] Plural G2's in —Si(G2)(G2)(G2) are be the same or different.

[0295] Plural G3's in —Si(G3)(G3)(G3) are the same or different.

[0296] Plural G6's in —Si(G6)(G6)(G6) are be the same or different.“Group Represented by —O—(R904)”

[0297] Specific examples of the group represented by —O—(R904) in this specification (specific example group G8) include:

[0298] —O(G1),

[0299] —O(G2),

[0300] —O(G3), and

[0301] —O(G6).

[0302] G1 is the “substituted or unsubstituted aryl group” described in the specific example group G1.

[0303] G2 is the “substituted or unsubstituted heterocyclic group” described in the specific example group G2.

[0304] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0305] G6 is the “substituted or unsubstituted cycloalkyl group” described in the specific example group G6.“Group Represented by —S—(R905)”

[0306] Specific examples of the group represented by —S—(R905) in this specification (specific example group G9) include:

[0307] —S(G1),

[0308] —S(G2),

[0309] —S(G3), and

[0310] —S(G6).

[0311] G1 is the “substituted or unsubstituted aryl group” described in the specific example group G1.

[0312] G2 is the “substituted or unsubstituted heterocyclic group” described in the specific example group G2.

[0313] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0314] G6 is the “substituted or unsubstituted cycloalkyl group” described in the specific example group G6.“Group Represented by —N(R906)(R907)”

[0315] Specific examples of the group represented by —N(R906)(R907) in this specification (specific example group G10) include:

[0316] —N(G1)(G1),

[0317] —N(G2)(G2),

[0318] —N(G1)(G2),

[0319] —N(G3)(G3), and

[0320] —N(G6)(G6).

[0321] G1 is the “substituted or unsubstituted aryl group” described in the specific example group G1.

[0322] G2 is the “substituted or unsubstituted heterocyclic group” described in the specific example group G2.

[0323] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0324] G6 is the “substituted or unsubstituted cycloalkyl group” described in the specific example group G6.

[0325] Plural G1's in —N(G1)(G1) are the same or different.

[0326] Plural G2's in —N(G2)(G2) are the same or different.

[0327] Plural G3's in —N(G3)(G3) are the same or different.

[0328] Plural G6's in —N(G6)(G6) are the same or different.“Halogen Atom”

[0329] Specific examples of the “halogen atom” described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like.“Substituted or Unsubstituted Fluoroalkyl Group”

[0330] The “substituted or unsubstituted fluoroalkyl group” described in this specification is a group in which at least one hydrogen atom bonded with a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is substituted by a fluorine atom, and includes a group in which all hydrogen atoms bonded with a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” are substituted by a fluorine atom (a perfluoro group). The number of carbon atoms of the “unsubstituted fluoroalkyl group” is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise specified in this specification. The “substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of the “fluoroalkyl group” are substituted by a substituent. The “substituted fluoroalkyl group” described in this specification also includes a group in which one or more hydrogen atoms bonded with a carbon atom of the alkyl chains in the “substituted fluoroalkyl group” are further substituted by a substituent, and a group in which one or more hydrogen atom of a substituent in the “substituted fluoroalkyl group” are further substituted by a substituent. Specific examples of the “unsubstituted fluoroalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (specific group G3) are substituted by a fluorine atom, and the like.“Substituted or Unsubstituted Haloalkyl Group”

[0331] The “substituted or unsubstituted haloalkyl group” described in this specification is a group in which at least one hydrogen atom bonded with a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is substituted by a halogen atom, and also includes a group in which all hydrogen atoms bonded with a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” are substituted by a halogen atom. The number of carbon atoms of the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise specified in this specification. The “substituted haloalkyl group” means a group in which one or more hydrogen atoms of the “haloalkyl group” are substituted by a substituent. The “substituted haloalkyl group” described in this specification also includes a group in which one or more hydrogen atoms bonded with a carbon atom of the alkyl chain in the “substituted haloalkyl group” are further substituted by a substituent, and a group in which one or more hydrogen atoms of a substituent in the “substituted haloalkyl group” are further substituted by a substituent. Specific examples of the “unsubstituted haloalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted by a halogen atom, and the like. A haloalkyl group is sometimes referred to as an alkyl halide group.“Substituted or Unsubstituted Alkoxy Group”

[0332] Specific examples of the “substituted or unsubstituted alkoxy group” described in this specification include a group represented by —O(G3), wherein G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3. The number of carbon atoms of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise specified in this specification.“Substituted or Unsubstituted Alkylthio Group”

[0333] Specific examples of the “substituted or unsubstituted alkylthio group” described in this specification include a group represented by —S(G3), wherein G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3. The number of carbon atoms of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise specified in this specification.“Substituted or Unsubstituted Aryloxy Group”

[0334] Specific examples of the “substituted or unsubstituted aryloxy group” described in this specification include a group represented by —O(G1), wherein G1 is the “substituted or unsubstituted aryl group” described in the specific example group G1. The number of ring carbon atoms of the “unsubstituted aryloxy group” is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in this specification.“Substituted or Unsubstituted Arylthio Group”

[0335] Specific examples of the “substituted or unsubstituted arylthio group” described in this specification include a group represented by —S(G1), wherein G1 is a “substituted or unsubstituted aryl group” described in the specific example group G1. The number of ring carbon atoms of the “unsubstituted arylthio group” is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise specified in this specification.“Substituted or Unsubstituted Trialkylsilyl Group”

[0336] Specific examples of the “trialkylsilyl group” described in this specification include a group represented by —Si(G3)(G3)(G3), where G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3. Plural G3's in —Si(G3)(G3)(G3) are the same or different. The number of carbon atoms in each alkyl group of the “trialkylsilyl group” is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise specified in this specification.“Substituted or Unsubstituted Aralkyl Group”

[0337] Specific examples of the “substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), wherein G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3, and G1 is the “substituted or unsubstituted aryl group” described in the specific example group G1. Therefore, the “aralkyl group” is a group in which a hydrogen atom of the “alkyl group” is substituted by an “aryl group” as a substituent, and is one form of the “substituted alkyl group.” The “unsubstituted aralkyl group” is the “unsubstituted alkyl group” substituted by the “unsubstituted aryl group”, and the number of carbon atoms of the “unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, more preferably 7 to 18, unless otherwise specified in this specification.

[0338] Specific examples of the “substituted or unsubstituted aralkyl group” include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group, an α-naphthylmethyl group, a 1-α-naphthylethyl group, a 2-α-naphthylethyl group, a 1-α-naphthylisopropyl group, a 2-α-naphthylisopropyl group, a β-naphthylmethyl group, a 1-β-naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, a 2-β-naphthylisopropyl group, and the like.

[0339] Unless otherwise specified in this specification, examples of the substituted or unsubstituted aryl group described in this specification preferably include a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9′-spirobifluorenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, and the like.

[0340] Unless otherwise specified in this specification, examples of the substituted or unsubstituted heterocyclic groups described in this specification preferably include a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an azadibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, a phenyldibenzothiophenyl group, and the like.

[0341] In this specification, the carbazolyl group is specifically each of the following groups, unless otherwise specified in this specification.

[0342] In this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0343] In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding site.

[0344] In this specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0345] In the general formulas (TEMP-34) to (TEMP-41), * represents a bonding site.

[0346] The substituted or unsubstituted alkyl group described in this specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a t-butyl group, or the like, unless otherwise specified in this specification.“Substituted or Unsubstituted Arylene Group”

[0347] The “substituted or unsubstituted arylene group” described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring of the “substituted or unsubstituted aryl group”, unless otherwise specified. Specific examples of the “substituted or unsubstituted arylene group” (specific example group G 12) include a divalent group derived by removing one hydrogen atom on the aryl ring of the “substituted or unsubstituted aryl group” described in the specific example group G1, and the like.“Substituted or Unsubstituted Divalent Heterocyclic Group”

[0348] The “substituted or unsubstituted divalent heterocyclic group” described in this specification is a divalent group derived by removing one hydrogen atom on the heterocycle of the “substituted or unsubstituted heterocyclic group”, unless otherwise specified. Specific examples of the “substituted or unsubstituted divalent heterocyclic group” (specific example group G13) include a divalent group derived by removing one hydrogen atom on the heterocycle of the “substituted or unsubstituted heterocyclic group” described in the specific example group G2, and the like.“Substituted or Unsubstituted Alkylene Group”

[0349] The “substituted or unsubstituted alkylene group” described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain of the “substituted or unsubstituted alkyl group”, unless otherwise specified. Specific examples of the “substituted or unsubstituted alkylene group” (specific example group G14) include a divalent group derived by removing one hydrogen atom on the alkyl chain of the “substituted or unsubstituted alkyl group” described in the specific example group G3, and the like.

[0350] The substituted or unsubstituted arylene group described in this specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.

[0351] In the general formulas (TEMP-42) to (TEMP-52), Q1 to Q10 are independently a hydrogen atom or a substituent.

[0352] In the general formulas (TEMP-42) to (TEMP-52), * represents a bonding site.

[0353] In the general formulas (TEMP-53) to (TEMP-62), Q1 to Q10 are independently a hydrogen atom or a substituent.

[0354] Q9 and Q10 may be bonded with each other via a single bond to form a ring.

[0355] In the general formulas (TEMP-53) to (TEMP-62), * represents a bonding site.

[0356] In the general formulas (TEMP-63) to (TEMP-68), Q1 to Q3 are independently a hydrogen atom or a substituent.

[0357] In the general formulas (TEMP-63) to (TEMP-68), * represents a bonding site.

[0358] The substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any group of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.

[0359] In the general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are independently a hydrogen atom or a substituent.

[0360] In the general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are independently a hydrogen atom or a substituent.

[0361] The above is the explanation of the “Substituent described in this specification.”“The Case where Bonded with Each Other to Form a Ring”

[0362] In this specification, the case where “one or more sets of adjacent two or more form a substituted or unsubstituted monocycle by bonding with each other, form a substituted or unsubstituted fused ring by bonding with each other, or do not bond with each other” means the case where “one or more sets of adjacent two or more form a substituted or unsubstituted monocycle by bonding with each other”; the case where “one or more sets of adjacent two or more form a substituted or unsubstituted fused ring by bonding with each other”; and the case where “one or more sets of adjacent two or more do not bond with each other.”

[0363] The case where “one or more sets of adjacent two or more form a substituted or unsubstituted monocycle by bonding with each other” and the case where “one or more sets of adjacent two or more form a substituted or unsubstituted fused ring by bonding with each other” in this specification (these cases may be collectively referred to as “the case where forming a ring by bonding with each other”) will be described below. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the mother skeleton is an anthracene ring will be described as an example.

[0364] For example, in the case where “one or more sets of adjacent two or more among R921 to R930 form a ring by bonding with each other”, the one set of adjacent two includes a pair of R921 and R922, a pair of R922 and R923, a pair of R923 and R924, a pair of R924 and R930, a pair of R930 and R925, a pair of R925 and R926, a pair of R926 and R927, a pair of R927 and R928, a pair of R928 and R929, and a pair of R929 and R921.

[0365] The “one or more sets” means that two or more sets of the adjacent two or more sets may form a ring at the same time. For example, R921 and R922 form a ring QA by bonding with each other, and at the same, time R925 and R926 form a ring QB by bonding with each other, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0366] The case where the “set of adjacent two or more” form a ring includes not only the case where the set (pair) of adjacent “two” is bonded with as in the above-mentioned examples, but also the case where the set of adjacent “three or more” are bonded with each other. For example, it means the case where R921 and R922 form a ring QA by bonding with each other, and R922 and R923 form a ring Qc by bonding with each other, and adjacent three (R921, R922 and R923) form rings by bonding with each other and together fused to the anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), the ring QA and the ring Qc share R922.

[0367] The “monocycle” or “fused ring” formed may be a saturated ring or an unsaturated ring, as a structure of the formed ring alone. Even when the “one pair of adjacent two” forms a “monocycle” or a “fused ring”, the “monocycle” or the “fused ring” may form a saturated ring or an unsaturated ring. For example, the ring QA and the ring QB formed in the general formula (TEMP-104) are independently a “monocycle” or a “fused ring.” The ring QA and the ring Qc formed in the general formula (TEMP-105) are “fused ring.” The ring QA and ring Qc of the general formula (TEMP-105) are fused ring by fusing the ring QA and the ring Qc together. When the ring QA of the general formula (TMEP-104) is a benzene ring, the ring QA is a monocycle. When the ring QA of the general formula (TMEP-104) is a naphthalene ring, the ring QA is a fused ring.

[0368] The “unsaturated ring” includes, in addition to an aromatic hydrocarbon ring and an aromatic heterocycle, an aliphatic hydrocarbon ring with an unsaturated bond, i.e., double and / or triple bonds in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and a non-aromatic heterocycle with an unsaturated bond (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). The “saturated ring” includes an aliphatic hydrocarbon ring without an unsaturated bond and a non-aromatic heterocycle without ab unsaturated bond.

[0369] Specific examples of the aromatic hydrocarbon ring include a structure in which the group listed as a specific example in the specific example group G1 is terminated by a hydrogen atom.

[0370] Specific examples of the aromatic heterocycle include a structure in which the aromatic heterocyclic group listed as a specific example in the example group G2 is terminated by a hydrogen atom.

[0371] Specific examples of the aliphatic hydrocarbon ring include a structure in which the group listed as a specific example in the specific example group G6 is terminated by a hydrogen atom.

[0372] The term “to form a ring” means forming a ring only with plural atoms of the mother skeleton, or with plural atoms of the mother skeleton and one or more arbitrary atoms in addition. For example, the ring QA shown in the general formula (TEMP-104), which is formed by bonding R921 and R922 with each other, is a ring formed from the carbon atom of the anthracene skeleton with which R921 is bonded, the carbon atom of the anthracene skeleton with which R922 is bonded, and one or more arbitrary atoms. For example, in the case where the ring QA is formed with R921 and R922, when a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton with which R921 is bonded, the carbon atom of the anthracene skeleton with which R922 is bonded, and four carbon atoms, the ring formed with R921 and R922 is a benzene ring.

[0373] Here, the “arbitrary atom” is preferably at least one atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, unless otherwise specified in this specification. In the arbitrary atom (for example, a carbon atom or a nitrogen atom), a bond which does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with “arbitrary substituent” described below. When an arbitrary atom other than a carbon atom is contained, the ring formed is a heterocycle.

[0374] The number of “one or more arbitrary atom(s)” constituting a monocycle or a fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less, unless otherwise specified in this specification.

[0375] The “monocycle” is preferable among the “monocycle” and the “fused ring”, unless otherwise specified in this specification.

[0376] The “unsaturated ring” is preferable among the “saturated ring” and the “unsaturated ring”, unless otherwise specified in this specification.

[0377] Unless otherwise specified in this specification, the “monocycle” is preferably a benzene ring.

[0378] Unless otherwise specified in this specification, the “unsaturated ring” is preferably a benzene ring.

[0379] Unless otherwise specified in this specification, when “one or more sets of adjacent two or more” are “bonded with each other to form a substituted or unsubstituted monocycle” or “bonded with each other to form a substituted or unsubstituted fused ring”, this specification, one or more sets of adjacent two or more are preferably bonded with each other to form a substituted or unsubstituted “unsaturated ring” from plural atoms of the mother skeleton and one or more and 15 or less atoms which is at least one kind selected from a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom.

[0380] The substituent in the case where the above-mentioned “monocycle” or “fused ring” has a substituent is, for example, an “arbitrary substituent” described below. Specific examples of the substituent which the above-mentioned “monocycle” or “fused ring” has include the substituent described above in the “Substituent described in this specification” section.

[0381] The substituent in the case where the above-mentioned “saturated ring” or “unsaturated ring” has a substituent is, for example, an “arbitrary substituent” described below. Specific examples of the substituent which the above-mentioned “monocycle” or “fused ring” has include the substituent described above in the “Substituent described in this specification” section.

[0382] The foregoing describes the case where “one or more sets of adjacent two or more form a substituted or unsubstituted monocycle by bonding with each other” and the case where “one or more sets of adjacent two or more form a substituted or unsubstituted fused ring by bonding with each other” (the case where “forming a ring by bonding with each other”).Substituent in the Case of “Substituted or Unsubstituted”

[0383] In one embodiment in this specification, the substituent (in this specification, sometimes referred to as an “arbitrary substituent”) in the case of “substituted or unsubstituted” is, for example, a group selected from the group consisting of:

[0384] an unsubstituted alkyl group including 1 to 50 carbon atoms,

[0385] an unsubstituted alkenyl group including 2 to 50 carbon atoms,

[0386] an unsubstituted alkynyl group including 2 to 50 carbon atoms,

[0387] an unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,

[0388] —Si(R901)(R902)(R903),

[0389] —O—(R904),

[0390] —S—(R905),

[0391] —N(R906)(R907),

[0392] a halogen atom, a cyano group, a nitro group,

[0393] an unsubstituted aryl group including 6 to 50 ring carbon atoms, and

[0394] an unsubstituted heterocyclic group including 5 to 50 ring atoms,

[0395] wherein, R901 to R907 are independently

[0396] a hydrogen atom,

[0397] a substituted or unsubstituted alkyl group including 1 to 50 carbon atoms,

[0398] a substituted or unsubstituted cycloalkyl group including 3 to 50 ring carbon atoms,

[0399] a substituted or unsubstituted aryl group including 6 to 50 ring carbon atoms, or

[0400] a substituted or unsubstituted heterocyclic group including 5 to 50 ring atoms.

[0401] When two or more R901's are present, the two or more R901's may be the same or different.

[0402] When two or more R902's are present, the two or more R902's may be the same or different.

[0403] When two or more R903's are present, the two or more R903's may be the same or different.

[0404] When two or more R904's are present, the two or more R904's may be the same or different.

[0405] When two or more R905's are present, the two or more R905's may be the same or different.

[0406] When two or more R906's are present, the two or more R906's may be the same or different.

[0407] When two or more R907's are present, the two or more R907's may be the same or different.

[0408] In one embodiment, the substituent in the case of “substituted or unsubstituted” is a group selected from the group consisting of:

[0409] an alkyl group including 1 to 50 carbon atoms,

[0410] an aryl group including 6 to 50 ring carbon atoms, and

[0411] a heterocyclic group including 5 to 50 ring atoms.

[0412] In one embodiment, the substituent in the case of “substituted or unsubstituted” is a group selected from the group consisting of:

[0413] an alkyl group including 1 to 18 carbon atoms,

[0414] an aryl group including 6 to 18 ring carbon atoms, and

[0415] a heterocyclic group including 5 to 18 ring atoms.

[0416] Specific examples of each of the arbitrary substituents include specific examples of substituent described in the section “Substituent described in this specification” above.

[0417] Unless otherwise specified in this specification, adjacent arbitrary substituents may form a “saturated ring” or an “unsaturated ring”, preferably form a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably form a benzene ring.

[0418] Unless otherwise specified in this specification, the arbitrary substituent may further have a substituent. The substituent which the arbitrary substituent further has is the same as that of the above-mentioned arbitrary substituent.

[0419] In this specification, the numerical range represented by “AA to BB” means the range including the numerical value AA described on the front side of “AA to BB” as the lower limit and the numerical value BB described on the rear side of “AA to BB” as the upper limit.New Compound

[0420] A compound according to an aspect of the present invention is represented by the following formula (1):wherein in the formula (1),X1 and X2 are independently N or CH; any one of X1 and X2 is N;Ar1 and Ar2 are independently

[0423] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0424] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

[0425] L1 to L3 are independently

[0426] a single bond,

[0427] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0428] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;

[0429] n1 is integer 0 to 4; when n1 is 0, (L1)n1 is single bond; when a plurality of L1's is present, the plurality of L1's may be the same as or different from each other;

[0430] n2 is integer 0 to 4; when n2 is 0, (L2)n2 is single bond; when a plurality of L2's is present, the plurality of L2's may be the same as or different from each other;

[0431] n3 is integer 0 to 4; when n3 is 0, (L3)n3 is single bond; when a plurality of L3's is present, the plurality of L3's may be the same as or different from each other;

[0432] R11 to R19 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R11 to R19 does not bond with each other;

[0433] R21 and R22 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form the substituted or unsubstituted, saturated or unsaturated ring;

[0434] R21 and R22 which do not form the substituted or unsubstituted, saturated or unsaturated ring are independently

[0435] a hydrogen atom,

[0436] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[0437] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;

[0438] the substituent R is selected from the group consisting of

[0439] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0440] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0441] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0442] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0443] —Si(R901)(R902)(R903),

[0444] —O—(R904),

[0445] —S—(R905),

[0446] —N(R906)(R907),

[0447] a halogen atom, a cyano group, a nitro group,

[0448] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0449] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

[0450] R901 to R907 are independently

[0451] a hydrogen atom,

[0452] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0453] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0454] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0455] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;

[0456] when two or more of each of R901 to R907 are present, the two or more of each of R901 to R907 may be the same as or different from each other; and

[0457] when two or more substituents R are present, the two or more substituents R may be the same as or different from each other.

[0458] In the formula (1), any one of X1 and X2 is N and the other is CH. That is, when X1 is N, X2 is CH. When X2 is N, X1 is CH.

[0459] In the formula (1), when a plurality of L1's is present (when n1 is 2 or more), Ar1 is bonded with L1 which is farthest from the nitrogen-containing six-membered ring containing X1 and X2. Similarly, when a plurality of L2's is present (when n2 is 2 or more), Ar2 is bonded with L2 which is farthest from the nitrogen-containing six-membered ring containing X1 and X2. Similarly, when a plurality of L3's is present (when n3 is 2 or more), the benzofluorene skeleton is bonded with L3 which is farthest from the nitrogen-containing six-membered ring containing X1 and X2.

[0460] For example, when n1 is 2, n2 is 3, and n3 is 2, the compound represented by the formula (1) is the following configuration. The “nitrogen-containing six-membered ring containing X1 and X2” is shown as ring α.

[0461] In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (11):wherein in the formula (11),X1, X2, Ar1, Ar2, L1, L2, n1, n2, R11 to R19, R21, and R22 are the same as defined in the formula (1).In one embodiment, R21 and R22 in the formula (11) do not form the substituted or unsubstituted, saturated or unsaturated ring.

[0464] In one embodiment, R21 and R22 in the formula (11) are a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0465] In one embodiment, R21 and R22 in the formula (11) are methyl groups.

[0466] In one embodiment, in the formula (11), X1 is N, and X2 is CH.

[0467] In one embodiment, the compound represented by the formula (11) is a compound represented by any one of the following formulas (111) to (113):wherein in the formula (111),L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);R111 to R120 is independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R111 to R120 does not bond with each other;

[0470] in the formula (112),

[0471] L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);

[0472] Y1 is N(R129), C(R130a)(R130b), O, or S;

[0473] any one of R121 to R129 represents a bond with L2;

[0474] R121 to R129 which do not represent a bond with L2 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R121 to R129 which do not represent a bond with L2 does not bond with each other;

[0475] R130a and R130b form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form the substituted or unsubstituted, saturated or unsaturated ring;

[0476] R130a and R130b which do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom or a substituent R;

[0477] R131 to R135 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R131 to R135 does not bond with each other;

[0478] in the formula (113),

[0479] L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);

[0480] any one of R141 to R150 represents a bond with L2;

[0481] R141 to R150 which do not represent a bond with L2 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R141 to R150 which do not represent a bond with L2 does not bond with each other;

[0482] R151 to R155 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R151 to R155 does not bond with each other; and

[0483] the substituent R is the same as defined in the formula (1).

[0484] In one embodiment, R123 in the formula (112) represents a bond with L2.

[0485] When R123 represents a bond with L2, the compound represented by the formula (112) is the following structure.

[0486] In one embodiment, Y1 is O.

[0487] In one embodiment, R141, R143, or R149 in the formula (113) represents a bond with L2.

[0488] In one embodiment, in the formula (11), X1 is CH, and X2 is N.

[0489] In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (21):wherein in the formula (21),X1, X2, Ar1, Ar2, L1, L2, n1, n2, R11 to R19, R21, and R22 are the same as defined in the formula (1);L21 is

[0492] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[0493] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; and

[0494] n21 is an integer 1 to 4; when a plurality of L21's is present, the plurality of L21's may be the same as or different from each other.

[0495] In one embodiment, R21 and R22 in the formula (21) do not form the substituted or unsubstituted, saturated or unsaturated ring.

[0496] In one embodiment, R21 and R22 in the formula (21) are a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms.

[0497] In one embodiment, R21 and R22 in the formula (21) are methyl groups.

[0498] In one embodiment, L21 in the formula (21) is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0499] In one embodiment, L21 in the formula (21) is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0500] In one embodiment, in the formula (21), X1 is N, and X2 is CH.

[0501] In one embodiment, the compound represented by the formula (21) is a compound represented by the following formula (211) or (212):wherein in the formula (211),Ar1, Ar2, L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);R211 to R214 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R211 to R214 does not bond with each other;

[0504] in the formula (212),

[0505] Ar1, Ar2, L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);

[0506] R221 to R226 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R221 to R226 does not bond with each other; and

[0507] the substituent R is the same as defined in the formula (1).

[0508] In one embodiment, in the formula (21), X1 is CH, and X2 is N.

[0509] In one embodiment, the compound represented by the formula (21) is a compound represented by the following formula (221) or (222):wherein in the formula (221),Ar1, Ar2, L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);R211 to R214 is independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R211 to R214 does not bond with each other;

[0512] in the formula (222),

[0513] Ar1, Ar2, L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);

[0514] R221 to R226 is independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R221 to R226 does not bond with each other; and

[0515] the substituent R is the same as defined in the formula (1).

[0516] In one embodiment, Ar1 and Ar2 in the formula (21) are independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 18 ring atoms.

[0517] In one embodiment, Ar1 and Ar2 in the formula (21) are independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0518] In one embodiment, L1 and L2 in the formula (1) are independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0519] In one embodiment, R11 to R19 in the formula (1) are hydrogen atoms.

[0520] In one embodiment, in the formula (1), the substituent in the case of “substituted or unsubstituted”, and the substituent R are a group selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a monovalent heterocyclic group having 5 to 50 ring atoms.

[0521] In one embodiment, in the formula (1), the substituent in the case of “substituted or unsubstituted”, and the substituent R are a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a monovalent heterocyclic group having 5 to 18 ring atoms.

[0522] In one embodiment, the compound represented by the formula (1) has at least one deuterium atom as the hydrogen atom within a molecular thereof.

[0523] In the present specification, the expression “has a deuterium atom as the hydrogen atom” means that the amount of the deuterium atom in the hydrogen atom is greater than the natural abundance based on the total amount of the protium atom and the deuterium atom. It can be confirmed by using a nuclear magnetic resonator that the amount of the deuterium atom is greater than the natural abundance based on the total amount of the protium atom and the deuterium atom.

[0524] In one embodiment, the compound represented by the formula (1) does not have a deuterium atom as the hydrogen atom within a molecular thereof.

[0525] In the present specification, the expression “does not have a deuterium atom as the hydrogen atom” means that the amount of the deuterium atom in all the hydrogen atoms within a molecular thereof is below the natural abundance based on the total amount of the protium atom and the deuterium atom. In other words, the compound represented by the formula (1) which does not have a deuterium atom as the hydrogen atom within a molecular thereof may have a deuterium atom with the amount below the natural abundance.

[0526] The amount of the protium atom can be confirmed by using a nuclear magnetic resonator.

[0527] In one embodiment, Ar1 in the formula (1) has at least one deuterium atom as the hydrogen atom.

[0528] In one embodiment, Ar2 in the formula (1) has at least one deuterium atom as the hydrogen atom.

[0529] In one embodiment, L3 in the formula (1) has at least one deuterium atom as the hydrogen atom.

[0530] In one embodiment, in the formula (1), at least one of, R11 to R19, R21, and R22 which are hydrogen atom, and hydrogen atoms possessed by R11 to R19, R21, and R22 which are the substituent R is a deuterium atom.

[0531] In one embodiment, L23 in the formula (1) does not have a deuterium atom as the hydrogen atom.

[0532] In one embodiment, in the formula (1),

[0533] R11 to R19 which are hydrogen atom, and

[0534] hydrogen atoms possessed by R11 to R19 which are the substituent R

[0535] are protium atoms.

[0536] In one embodiment, in the formula (1), R21 and R22 are independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and hydrogen atoms possessed by R21 and R22 are protium atoms.

[0537] The compound represented by the formula (1) can be synthesized in accordance with Examples by using known alternative reactions or raw materials adapted to the target compound.

[0538] Specific examples of the compound represented by the formula (1) will be described below, but these are merely examples, and the compound represented by the formula (1) is not limited to the following specific examples.[Material for Organic Electroluminescence Device]The compound according to an aspect of the present invention is useful as a material for an organic EL device, and for example, is useful as an electron-transporting region for an organic EL device.[Organic EL Device]An organic EL device according to an aspect of the present invention is described.The organic EL device according to an aspect of the present invention includes a cathode, an anode and one or two or more organic layers arranged between the cathode and the anode, wherein at least one layer of the organic layers includes the compound according to an aspect of the present invention (the compound represented by the formula (1)).In one embodiment, the organic EL device according to an aspect of the present invention includes an anode, an emitting layer, an electron-transporting region, and a cathode in this order, wherein the electron-transporting region includes the compound according to an aspect of the present invention (the compound represented by the formula (1)).In one embodiment, the electron-transporting region includes a first layer (also referred to as “first electron-transporting layer” or “hole-barrier layer”) and a second layer (also referred to as “second electron-transporting layer”) in this order from the emitting layer side, and the first layer includes the compound represented by the formula (1). For example, the configuration of the electron-transporting layer described later can be applied as the second layer in this case.As a representative device configuration of the organic EL device, structures in which the following structures are stacked on a substrate can be given:(1) an anode / an emitting layer / an electron-transporting region / a cathode(2) an anode / a hole-transporting region / an emitting layer / an electron-transporting region / a cathodewherein “ / ” indicates that the layers are stacked adjacent to each other.The electron-transporting region is generally composed of one or more layer selected from an electron-injecting layer and an electron-transporting layer. The hole-transporting region is generally composed of one or more layer selected from a hole-injecting layer and a hole-transporting layer.A schematic configuration of the organic EL device according to an aspect of the present invention will be described with reference to FIG. 1.The organic EL device 1 according to an aspect of the present invention includes a substrate 2, an anode 3, an emitting layer 5, a cathode 10, a hole-transporting region 4 between the anode 3 and the emitting layer 5, and an electron-transporting region 6 between the emitting layer 5 and the cathode 10.Members which can be used in the organic EL device according to an aspect of the present invention, materials for forming each layer, other than the above-mentioned compounds, and the like, will be described below.(Substrate)The substrate is used as a support of an emitting device. As the substrate, glass, quartz, plastic or the like can be used, for example. Further, a flexible substrate may be used. The term “flexible substrate” means a bendable (flexible) substrate, and specific examples thereof include a plastic substrate formed of polycarbonate, polyvinyl chloride or the like.(Anode)For the anode formed on the substrate, metals, alloys, electrically conductive compounds, mixtures thereof, and the like, which have large work function (specifically 4.0 eV or more) are preferably used. Specific examples thereof include indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, and the like. In addition thereto, specific examples thereof include gold (Au), platinum (Pt), a nitride of a metallic material (for example, titanium nitride), or the like.(Hole-Injecting Layer)The hole-injecting layer is a layer containing a substance having high hole-injecting property. As the substance having high hole-injecting property, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, an aromatic amine compound, a polymer compound (oligomers, dendrimers, polymers, and the like), or the like can be given.(Hole-Transporting Layer)The hole-transporting layer is a layer containing a substance having high hole-transporting property. For the hole-transporting layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. A polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. Provided that a substance other than the above-described substances may be used as long as the substance has higher hole-transporting property than electron-transporting property. The layer containing the substance having high hole-transporting property may be not only a single layer, but also layers in which two or more layers formed of the above-described substances are stacked.(Guest (Dopant) Material of Emitting Layer)The emitting layer is a layer containing a substance having high luminous property, and various materials can be used. For example, as the substance having high emitting property, a fluorescent compound which emits fluorescence or a phosphorescent compound which emits phosphorescence can be used. The fluorescent compound is a compound which can emit from a singlet excited state, and the phosphorescent compound is a compound which can emit from a triplet excited state.

[0557] As a blue fluorescent emitting material which can be used for the emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, and the like can be used. As a green fluorescent emitting material which can be used for the emitting layer, aromatic amine derivatives and the like can be used. As a red fluorescent emitting material which can be used for the emitting layer, tetracene derivatives, diamine derivatives and the like can be used.

[0558] As a blue phosphorescent emitting material which can be used for the emitting layer, metal complexes such as iridium complexes, osmium complexes and platinum complexes are used. As a green phosphorescent emitting material which can be used for the emitting layer, iridium complexes and the like are used. As a red phosphorescent emitting material which can be used for the emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes and europium complexes are used.(Host Material for Emitting Layer)

[0559] The emitting layer may have a constitution in which the substance having high emitting property (guest material) is dispersed in another substance (host material). As a substance for dispersing the substance having high emitting property, a variety of substances can be used, and it is preferable to use a substance having a higher lowest unoccupied molecular orbital level (LUMO level) and a lower highest occupied molecular orbital level (HOMO level) than a substance having high emitting property.

[0560] As a substance (host material) for dispersing the substance having high emitting property, 1) a metal complex such as an aluminum complex, a beryllium complex, and a zinc complex, 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, and a phenanthroline derivative, 3) a fused aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, and a chrysene derivative, and 4) an aromatic amine compound such as a triarylamine derivative and a fused polycyclic aromatic amine derivative are used.(Electron-Transporting Layer)

[0561] The electron-transporting layer is a layer containing a substance having high electron-transporting property. For the electron-transporting layer, 1) a metal complex such as an aluminum complex, a beryllium complex, and a zinc complex; 2) a heteroaromatic complex such as an imidazole derivative, a benzimidazole derivative, an azine derivative, carbazole derivative, and a phenanthroline derivative; and 3) a polymer compound can be used.

[0562] In an aspect of the present invention, the electron-transporting layer may include or may not include another substance described above in addition to the compound (the compound represented by the formula (1)) according to an aspect of the present invention.(Electron-Injecting Layer) The electron-injecting layer is a layer containing a substance having high electron-injecting property. For the electron-injecting layer, lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), a metal complex compound such as 8-hydroxyquinolinolato-lithium (Liq), an alkali metal such as lithium oxide (LiOx), an alkaline earth metal, or a compound thereof can be used.(Cathode)

[0563] For the cathode, metals, alloys, electrically conductive compounds, mixtures thereof, and the like, which have small work function (specifically 3.8 eV or less) are preferably used. Specific examples of such a cathode material include an element belonging to Group 1 or Group 2 of the Periodic Table of the Elements, i.e., an alkali metal such as lithium (L1) and cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), and an alloy containing these (e.g., MgAg and AlLi); a rare earth metal such as europium (Eu) and ytterbium (Yb), and an alloy containing these.

[0564] The cathode is usually formed by a vacuum deposition method or a sputtering meth od. Further, when silver paste or the like is used, it is possible to use the coating method, the inkjet method or the like.

[0565] When the electron-injecting layer is provided, the cathode can be formed using various conductive materials such as aluminum, silver, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the work function value.

[0566] In the organic EL device according to an aspect of the present invention, the thickness of each layer is not particularly limited, but is normally preferable several nm to 1 μm generally in order to suppress defects such as pinholes, to suppress applied voltages to be low, and to improve luminous efficiency.

[0567] In the organic EL device according to an aspect of the present invention, the method for forming each layer is not particularly limited. A conventionally-known method for forming each layer such as a vacuum deposition process and a spin coating process can be used. Each layer such as the emitting layer can be formed by a known method such as a vacuum deposition process, a molecular beam deposition process (MBE process), or an application process such as a dipping process, a spin coating process, a casting process, a bar coating process and a roll coating process, using a solution prepared by dissolving the material in a solvent.[Electronic Apparatus]

[0568] An electronic apparatus according to an aspect of the present invention is characterized by including the organic EL device according to an aspect of the present invention.

[0569] Specific examples of the electronic apparatus include display components such as an organic EL panel module; display devices for a television, a cellular phone and a personal computer; and emitting devices such as a light and a vehicular lamp; and the like.EXAMPLESCompound

[0570] Compounds represented by the formula (1) used in the fabrication of organic EL devices of Examples are shown below.

[0571] Compounds used in the fabrication of organic EL devices of Comparative Examples are shown below.

[0572] Other compounds used in the fabrication of the organic EL devices of Examples and Comparative Examples are shown below.Example 1<Fabrication of Organic EL Device>

[0573] An organic EL device was fabricated as follows.

[0574] A 25 mm×75 mm×1.1 mm-thick glass substrate with an ITO transparent electrode (anode) (manufactured by GEOMATEC Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then subjected to UV-ozone cleaning for 30 minutes. The ITO has the film thickness of 130 nm.

[0575] The glass substrate with the transparent electrode after being cleaned was mounted onto a substrate holder in a vacuum vapor deposition apparatus. First, compounds HTL-1 and HI-1 were co-deposited on the surface on the side where the transparent electrode was formed so as to cover the transparent electrode to be 3% by mass in a proportion of the compound HI-1 to form a hole-injecting layer having the thickness of 10 nm.

[0576] The compound HTL-1 was deposited on the hole-injecting layer to form a first hole-transporting layer having the thickness of 80 nm.

[0577] A compound EBL-1 was deposited on the first hole-transporting layer to form a second hole-transporting layer having the thickness of 5 nm.

[0578] A compound BH-1 (host material) and a compound BD-1 (dopant material) were co-deposited on the second hole-transporting layer to be 1% by mass in a proportion of the compound BD-1 to form an emitting layer having the thickness of 20 nm.

[0579] A compound ET-1 was deposited on the emitting layer to form a first electron-transporting layer (hole-barrier layer) having the thickness of 5 nm.

[0580] A compound ETL-1 and Liq were co-deposited on the first electron-transporting layer to be 50% by mass in a proportion of Liq to form a second electron-transporting layer having the thickness of 25 nm.

[0581] A metal Yb was deposited on the second electron-transporting layer to form an electron-injecting layer having the thickness of 1 nm.

[0582] A metal Al was deposited on the electron-injecting layer to form a cathode having the thickness of 80 nm.

[0583] The device configuration of the organic EL device of the Example 1 is schematically described as follows.

[0584] ITO (130) / HTL-1:HI-1 (10:3%) / HTL-1 (80) / EBL-1 (5) / BH-1:BD-1 (20:1%) / ET-1 (5) / ETL-1:Liq (25:50%) / Yb (1) / Al (80)

[0585] The numerical values in parentheses indicate film thickness (unit: nm). In addition, the numerical values represented by percentages in parentheses each indicate the proportion (% by mass) of the latter compound in the corresponding layer.<Evaluation of Organic EL Device>

[0586] The fabricated organic EL device was evaluated as follows. The results are shown in Table 1.External Quantum Efficiency (EQE)

[0587] A voltage was applied to the organic EL device so that the current density became 10 mA / cm2, and the EL emission spectrum was measured by using Spectroradiometer CS-2000 (manufactured by KONICA MINOLTA, INC.). EQE (%) was calculated from the obtained spectral emission luminance spectrum. EQE ratio (%) in Table 1 is used as a relative value when the value of Comparative Example 1 described later is 100.Examples 2 to 18 and Comparative Example 1

[0588] Organic EL devices were prepared and evaluated in the same manner as in Example 1, except that compounds shown in Table 1 were used instead of ET-1. The results are shown in Table 1.TABLE 1First electron-transporting layerEQE (%)EQE ratio (%)Example 1ET-110.1110Example 2ET-210.0110Example 3ET-39.7107Example 4ET-510.0110Example 5ET-610.1111Example 6ET-710.0110Example 7ET-89.7106Example 8ET-910.1111Example 9ET-1010.1110Example 10ET-1110.1111Example 11ET-1210.1111Example 12ET-1310.0110Example 13ET-149.9109Example 14ET-159.7107Example 15ET-169.8108Example 16ET-179.8108Example 17ET-1810.1110Example 18ET-1910.1111Comparative Example 1ET-Ref19.1100Example 19<Fabrication of Organic EL Device>

[0589] An organic EL device was fabricated as follows.

[0590] A 25 mm×75 mm×1.1 mm-thick glass substrate with an ITO transparent electrode (anode) (manufactured by GEOMATEC Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then subjected to UV-ozone cleaning for 30 minutes. The ITO has the film thickness of 130 nm.

[0591] The glass substrate with the transparent electrode after being cleaned was mounted onto a substrate holder in a vacuum vapor deposition apparatus. First, compounds HTL-2 and HI-1 were co-deposited on the surface on the side where the transparent electrode was formed so as to cover the transparent electrode to be 3% by mass in a proportion of the compound HI-1 to form a hole-injecting layer having the thickness of 10 nm.

[0592] The compound HTL-2 was deposited on the hole-injecting layer to form a first hole-transporting layer having the thickness of 80 nm.

[0593] A compound EBL-1 was deposited on the first hole-transporting layer to form a second hole-transporting layer having the thickness of 5 nm.

[0594] A compound BH-1 (host material) and a compound BD-1 (dopant material) were co-deposited on the second hole-transporting layer to be 1% by mass in a proportion of the compound BD-1 to form an emitting layer having the thickness of 20 nm.

[0595] A compound ET-6 was deposited on the emitting layer to form a first electron-transporting layer (hole-barrier layer) having the thickness of 5 nm.

[0596] A compound ETL-1 and Liq were co-deposited on the first electron-transporting layer to be 50% by mass in a proportion of Liq to form a second electron-transporting layer having the thickness of 25 nm.

[0597] A metal Yb was deposited on the second electron-transporting layer to form an electron-injecting layer having the thickness of 1 nm.

[0598] A metal Al was deposited on the electron-injecting layer to form a cathode having the thickness of 80 nm.

[0599] The device configuration of the organic EL device of the Example 19 is schematically described as follows.

[0600] ITO (130) / HTL-2:HI-1 (10:3%) / HTL-2 (80) / EBL-1 (5) / BH-1:BD-1 (20:1%) / ET-6 (5) / ETL-1:Liq (25:50%) / Yb (1) / Al (80)

[0601] The numerical values in parentheses indicate film thickness (unit: nm). In addition, the numerical values represented by percentages in parentheses each indicate the proportion (% by mass) of the latter compound in the corresponding layer.<Evaluation of Organic EL Device>

[0602] The fabricated organic EL device was evaluated in the same manner as in Example 1. The results are shown in Table 2. EQE ratio in Table 2 is used as a relative value when the value of Comparative Example 2 described later is 100.Examples 20 to 21 and Comparative Example 2

[0603] Organic EL devices were prepared and evaluated in the same manner as in Example 19, except that compounds shown in Table 2 were used instead of ET-6. The results are shown in Table 2.TABLE 2First electron-transporting layerEQE (%)EQE ratio (%)Example 19ET-610.2109Example 20ET-710.1107Example 21ET-910.3110Comparative Example 2ET-Ref29.4100Example 22<Fabrication of Organic EL Device>

[0604] An organic EL device was fabricated as follows.

[0605] A 25 mm×75 mm×1.1 mm-thick glass substrate with an ITO transparent electrode (anode) (manufactured by GEOMATEC Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then subjected to UV-ozone cleaning for 30 minutes. The ITO has the film thickness of 130 nm.

[0606] The glass substrate with the transparent electrode after being cleaned was mounted onto a substrate holder in a vacuum vapor deposition apparatus. First, compounds HTL-1 and HI-1 were co-deposited on the surface on the side where the transparent electrode was formed so as to cover the transparent electrode to be 3% by mass in a proportion of the compound HI-1 to form a hole-injecting layer having the thickness of 10 nm.

[0607] The compound HTL-3 was deposited on the hole-injecting layer to form a first hole-transporting layer having the thickness of 80 nm.

[0608] A compound EBL-1 was deposited on the first hole-transporting layer to form a second hole-transporting layer having the thickness of 5 nm.

[0609] A compound BH-2 (host material) and a compound BD-1 (dopant material) were co-deposited on the second hole-transporting layer to be 1% by mass in a proportion of the compound BD-1 to form an emitting layer having the thickness of 20 nm.

[0610] A compound ET-4 was deposited on the emitting layer to form a first electron-transporting layer (hole-barrier layer) having the thickness of 5 nm.

[0611] A compound ETL-1 and Liq were co-deposited on the first electron-transporting layer to be 50% by mass in a proportion of Liq to form a second electron-transporting layer having the thickness of 25 nm.

[0612] A metal Yb was deposited on the second electron-transporting layer to form an electron-injecting layer having the thickness of 1 nm.

[0613] A metal Al was deposited on the electron-injecting layer to form a cathode having the thickness of 80 nm.

[0614] The device configuration of the organic EL device of the Example 22 is schematically described as follows.

[0615] ITO (130) / HTL-1:HI-1 (10:3%) / HTL-3 (80) / EBL-1 (5) / BH-2:BD-1 (20:1%) / ET-4 (5) / ETL-1:Liq (25:50%) / Yb (1) / Al (80)

[0616] The numerical values in parentheses indicate film thickness (unit: nm). In addition, the numerical values represented by percentages in parentheses each indicate the proportion (% by mass) of the latter compound in the corresponding layer.<Evaluation of Organic EL Device>

[0617] The fabricated organic EL device was evaluated as follows. The results are shown in Table 3.Device Lifetime

[0618] A voltage was applied to the obtained organic EL device at room temperature so that the current density became 50 mA / cm2, and the time until the luminance became 95% of the initial luminance (LT95 (unit: h)) was measured. LT95 ratio (%) is used as a relative value when the value of Comparative Example 3 described later is 100.Comparative Example 3

[0619] An organic EL device was prepared and evaluated in the same manner as in Example 22, except that compounds shown in Table 3 were used instead of ET-4. The results are shown in Table 3.TABLE 3First electron-LT95transportingLT95ratiolayer(h)(%)Example 22ET-4153132ComparativeET-Ref3116100Example 3Synthesis of Compound(Synthesis Example 1) Synthesis of ET-1

[0620] ET-1 was synthesized through the synthetic route described below.

[0621] 4-chloro-2,6-diphenylpyrimidine (4.50 g), 2-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6.87 g), and (Amphos)2PdCl2 (0.30 g) were added to a flask. After the atmosphere in the flask was replaced with argon gas, 1,4-dioxane (169 mL), and 2 M of aqueous solution of sodium carbonate (21.1 mL) were added thereto, and it was heated and stirred under reflux condition for 6.5 hours. After the reaction solution was cooled, dichloromethane was added thereto, and the resulting solution was filtered through silica gel. The crude product obtained by distilling off the solvent was purified by silica gel chromatography and washed with hexane to obtain ET-1 as a white solid (7.45 g, 93% yield).

[0622] The mass spectrum thereof was analyzed as m / e=475 for a molecular weight of 474.61, and this white solid was identified as an intended product.(Synthesis Example 2) Synthesis of ET-2

[0623] ET-2 was synthesized through the synthetic route described below.

[0624] 4-([1,1′ biphenyl]-3-yl)-6-chloro-2-phenylpyrimidine (4.50 g), 2-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.87 g), Pd2(dba)3 (0.24 g), and SPhos (0.43 g) were added to a flask. After the atmosphere in the flask was replaced with argon gas, 1,4-dioxane (131 mL), and 2 M of aqueous solution of sodium carbonate (16.4 mL) were added thereto, and it was heated and stirred under reflux condition for 6 hours. After the reaction solution was cooled, dichloromethane was added thereto, and the resulting solution was filtered through silica gel. The crude product obtained by distilling off the solvent was purified by silica gel chromatography, and washed with hexane to obtain ET-2 as a white solid (5.66 g, 78% yield).

[0625] The mass spectrum thereof was analyzed as m / e=551 for a molecular weight of 550.71, and this white solid was identified as an intended product.(Synthesis Example 3) Synthesis of ET-3

[0626] ET-3 was synthesized through the synthetic route described below.

[0627] 4-([1,1′-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (4.07 g), 2-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.43 g), Pd2(dba)3 (0.18 g), and Amphos (0.21 g) were added to a flask. After the atmosphere in the flask was replaced with argon gas, 1,4-dioxane (67 mL), and 2 M of aqueous solution of sodium carbonate (15.0 mL) were added thereto, and it was heated and stirred under reflux condition for 6 hours. After the reaction solution was cooled, H2O was added thereto, and the resulting solution was extracted with dichloromethane. The crude product obtained by distilling off the solvent was purified by silica gel chromatography and recrystallization using toluene / hexane to obtain ET-3 as a white solid (2.90 g, 53% yield).

[0628] The mass spectrum thereof was analyzed as m / e=551 for a molecular weight of 550.71, and this white solid was identified as an intended product.(Synthesis Example 4) Synthesis of ET-4

[0629] ET-4 was synthesized through the synthetic route described below.

[0630] 4,6-dichloro-2-phenylpyrimidine (17.84 g), 2-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (14.68 g), and PdCl2(dppf)CH2Cl2 (1.30 g) were added to a flask. After the atmosphere in the flask was replaced with argon gas, toluene (317 mL), DME (79 mL), and 2 M of aqueous solution of sodium carbonate (59.5 mL) were added thereto, and it was heated and stirred under reflux condition for 6.5 hours. The reaction solution was cooled and filtered through silica gel. The crude product obtained by distilling off the solvent was purified by silica gel chromatography, and washed with hexane to obtain 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine as a white solid (13.37 g, 76% yield).

[0631] 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.30 g), 2-(4-(dibenzo[b,d]furan-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.23 g), and (Amphos)2PdCl2 (0.28 g) were added to a flask. After the atmosphere in the flask was replaced with argon gas, 1,4-dioxane (99 mL), and 2 M of aqueous solution of sodium carbonate (12.4 mL) were added thereto, and it was heated and stirred under reflux condition for 4 hours. After the reaction was cooled, MeOH was added thereto, and the precipitated solid was collected by filtration. The crude product was purified by silica gel chromatography, and washed with hexane to obtain ET-4 as a white solid (4.90 g, 77% yield).

[0632] The mass spectrum thereof was analyzed as m / e=641 for a molecular weight of 640.79, and this white solid was identified as an intended product.(Synthesis Example 5) Synthesis of ET-5

[0633] ET-5 was synthesized through the synthetic route described below.

[0634] 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.30 g), (3-(dibenzo[b,d]furan-2-yl)phenyl)boronic acid (3.72 g), and (Amphos)2PdCl2 (0.28 g) were added to a flask. After the atmosphere in the flask was replaced with argon gas, 1,4-dioxane (99 mL), and 2 M of aqueous solution of sodium carbonate (12.4 mL) were added thereto, and it was heated and stirred under reflux condition for 4 hours. After the reaction was cooled, MeOH was added thereto, and the precipitated solid was collected by filtration. The crude product was purified by silica gel chromatography, and washed with hexane to obtain ET-5 as a white solid (2.84 g, 45% yield).

[0635] The mass spectrum thereof was analyzed as m / e=641 for a molecular weight of 640.79, and this white solid was identified as an intended product.(Synthesis Example 6) Synthesis of ET-6

[0636] ET-6 was synthesized through the synthetic route described below.

[0637] 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-yl)pyrimidine (5.40 g), 5-bromo-7,7-dimethyl-7H-benzo[c]fluorene (3.78 g), and (Amphos)2PdCl2 (0.32 g) were added to a flask. After the atmosphere in the flask was replaced with argon gas, 1,4-dioxane (111 mL), and 2 M of aqueous solution of sodium carbonate (13.9 mL) was added thereto, and it was heated and stirred at 74° C. for 22 hours. The reaction solution was cooled and filtered through silica gel. The crude product obtained by distilling off the solvent was purified by silica gel chromatography to obtain ET-6 as a white solid (4.81 g, 71% yield).

[0638] The mass spectrum thereof was analyzed as m / e=601 for a molecular weight of 600.77, and this white solid was identified as an intended product.(Synthesis Example 7) Synthesis of ET-7

[0639] ET-7 was synthesized through the synthetic route described below.

[0640] 4-([1,1′ biphenyl]-3-yl)-2-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-yl)pyrimidine (7.00 g), 5-bromo-7,7-dimethyl-7H-benzo[c]fluorene (4.84 g), Pd2(dba)3 (0.23 g), and SPhos (0.41 g) were added to a flask. After the atmosphere in the flask was replaced with argon gas, 1,4-dioxane (125 mL), and 2 M of aqueous solution of sodium carbonate of (15.6 mL) were added thereto, and it was heated and stirred under reflux condition for 7 hours. The reaction solution was cooled and filtered through silica gel. The crude product obtained by distilling off the solvent was purified by silica gel chromatography, and washed with hexane to obtain ET-7 as a white solid (7.46 g, 88% yield).

[0641] The mass spectrum thereof was analyzed as m / e=677 for a molecular weight of 676.86, and this white solid was identified as an intended product.(Synthesis Example 8) Synthesis of ET-8

[0642] ET-8 was synthesized through the synthetic route described below.

[0643] 4-([1,1′ biphenyl]-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine (5.00 g), 2-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.79 g), Pd2(dba)3 (0.20 g), and SPhos (0.35 g) were added to a flask. After the atmosphere in the flask was replaced with argon gas, 1,4-dioxane (108 mL), and 2 M of aqueous solution of sodium carbonate (13.5 mL) were added thereto, and it was heated and stirred under reflux condition for 7 hours. The reaction solution was filtered through silica gel. The crude product obtained by distilling off the solvent was purified by silica gel chromatography, and washed with hexane to obtain ET-8 as a white solid (5.78 g, 85% yield).

[0644] The mass spectrum thereof was analyzed as m / e=627 for a molecular weight of 626.80, and this white solid was identified as an intended product.(Synthesis Example 9) Synthesis of ET-9

[0645] ET-9 was synthesized through the synthetic route described below.

[0646] 4,6-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-yl)pyrimidine (4.84 g), 5-bromo-7,7-dimethyl-7H-benzo[c]fluorene (3.23 g), Pd2(dba)3 (0.18 g), and SPhos (0.33 g) were added to a flask. It was replaced with argon gas, 1,4-dioxane (67 mL), and 2 M of aqueous solution of sodium carbonate (25 mL) were added thereto, and then it was heated and stirred under reflux condition for 7 hours. After the reaction solution was cooled, water and dichloromethane were added to extract the oil phase. The crude product obtained by distilling off the solvent was purified by silica gel chromatography and recrystallization using toluene to obtain ET-9 as a pale yellow solid (3.43 g, 57% yield).

[0647] The mass spectrum thereof was analyzed as m / e=601 for a molecular weight of 600.76, and it was identified as an intended product.(Synthesis Example 10) Synthesis of ET-10

[0648] ET-10 was synthesized through the synthetic route described below.

[0649] 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (9.80 g), 2-(9,9-dimethyl-9H-fluorene-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8.70 g), and Pd(PPh3)4 (0.52 g) were added to a flask. It was replaced with argon gas, DME (186 mL), and 2 M of aqueous solution of sodium carbonate (22.6 mL) was added thereto, and then it was heated and stirred under reflux condition for 19 hours. After the reaction solution was cooled, toluene was added to separate the reaction solution, and the oil phase was recovered. After distilling off the solvent, MeOH was added, and the precipitated solid was collected by filtration. The crude product was purified by silica gel chromatography, and washed with a mixed solvent of heptane and xylene to obtain ET-10 as a white solid (7.86 g, 58% yield).

[0650] The mass spectrum thereof was analyzed as m / e=591 for a molecular weight of 590.77, and it was identified as an intended product.(Synthesis Example 11) Synthesis of ET-11

[0651] ET-11 was synthesized through the synthetic route described below.

[0652] 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.33 g), (3-(naphthalene-1-yl)phenyl)boronic acid (2.60 g), and (Amphos)2PdCl2 (0.28 g) were added to a flask. It was replaced with argon gas, 1,4-dioxane (67 mL), and 2 M of aqueous solution of sodium carbonate (12.5 mL) were added thereto, and then it was heated and stirred under reflux condition for 7 hours. After the reaction solution was cooled, water and dichloromethane were added to separate the reaction solution, and the oil phase was extracted. The crude product obtained by distilling off the solvent was purified by silica gel chromatography to obtain ET-11 as a pale yellow solid (4.14 g, 69% yield).

[0653] The mass spectrum thereof was analyzed as m / e=601 for a molecular weight of 600.76, and it was identified as an intended product.(Synthesis Example 12) Synthesis of ET-12

[0654] ET-12 was synthesized through the synthetic route described below

[0655] 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.33 g), (3-(phenanthrene-9-yl)phenyl)boronic acid (3.13 g), and (Amphos)2PdCl2 (0.28 g) were added to a flask. It was replaced with argon gas, 1,4-dioxane (67 mL), and 2 M of aqueous solution of sodium carbonate (12.5 mL) were added thereto, and then it was heated and stirred under reflux condition for 7 hours. After the reaction solution was cooled, water and dichloromethane were added to separate the reaction solution, and the oil phase was extracted. The crude product obtained by distilling off the solvent was purified by silica gel chromatography to obtain ET-12 as a pale yellow solid (3.38 g, 52% yield).

[0656] The mass spectrum thereof was analyzed as m / e=651 for a molecular weight of 650.82, and it was identified as an intended product.(Synthesis Example 13) Synthesis of ET-13

[0657] ET-13 was synthesized through the synthetic route described below.

[0658] 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.33 g), (3-(phenanthrene-1-yl)phenyl)boronic acid (3.13 g), and (Amphos)2PdCl2 (0.28 g) were added to a flask. It was replaced with argon gas, 1,4-dioxane (67 mL), and 2 M of aqueous solution of sodium carbonate (12.5 mL) were added thereto, and then it was heated and stirred under reflux condition for 7 hours. After the reaction solution was cooled, water and dichloromethane were added to separate the reaction solution, and the oil phase was extracted. The crude product obtained by distilling off the solvent was purified by silica gel chromatography to obtain ET-13 as a pale yellow solid (3.78 g, 58% yield).

[0659] The mass spectrum thereof was analyzed as m / e=651 for a molecular weight of 650.82, and it was identified as an intended product.(Synthesis Example 14) Synthesis of ET-14

[0660] ET-14 was synthesized through the synthetic route described below.

[0661] 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.33 g), [1,1′:3′,1″-terphenyl]-5′-ylboronic acid (2.88 g), and (Amphos)2PdCl2 (0.28 g) were added to a flask. It was replaced with argon gas, 1,4-dioxane (67 mL), and 2 M of aqueous solution of sodium carbonate (12.5 mL) were added thereto, and then it was heated and stirred under reflux condition for 7 hours. After the reaction solution was cooled, water and dichloromethane were added to separate the reaction solution, and the oil phase was extracted. The crude product obtained by distilling off the solvent was purified by silica gel chromatography and recrystallization using toluene to obtain ET-14 as a white solid (4.38 g, 70% yield).

[0662] The mass spectrum thereof was analyzed as m / e=627 for a molecular weight of 626.80, and it was identified as an intended product.(Synthesis Example 15) Synthesis of ET-15

[0663] ET-15 was synthesized through the synthetic route described below.

[0664] 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.08 g), 4,4,5,5-tetramethyl-2-(phenanthrene-3-yl)-1,3,2-dioxaborolane (3.44 g), and (Amphos)2PdCl2 (0.27 g) were added to a flask. It was replaced with argon gas, 1,4-dioxane (94 mL), and 2 M of aqueous solution of sodium carbonate (14.1 mL) were added thereto, and then it was heated and stirred under reflux condition for 7 hours. After the reaction solution was cooled, water and dichloromethane were added to separate the reaction solution, and the oil phase was extracted. The crude product obtained by distilling off the solvent was purified by silica gel chromatography and recrystallization using toluene to obtain ET-15 as a pale yellow solid (2.55 g, 47% yield).

[0665] The mass spectrum thereof was analyzed as m / e=575 for a molecular weight of 574.72, and it was identified as an intended product.(Synthesis Example 16) Synthesis of ET-16

[0666] ET-16 was synthesized through the synthetic route described below.

[0667] 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.33 g), dibenzo[b,d]furan-2-ylboronic acid (2.22 g), and (Amphos)2PdCl2 (0.28 g) were added to a flask. It was replaced with argon gas, 1,4-dioxane (67 mL), and 2 M of aqueous solution of sodium carbonate (12.5 mL) were added thereto, and then it was heated and stirred under reflux condition for 7 hours. After the reaction solution was cooled, water was added thereto, and the precipitated solid was collected by filtration. The crude product was purified by silica gel chromatography to obtain ET-16 as a white solid (3.62 g, 64% yield).

[0668] The mass spectrum thereof was analyzed as m / e=565 for a molecular weight of 564.68, and it was identified as an intended product.(Synthesis Example 17) Synthesis of ET-17

[0669] ET-17 was synthesized through the synthetic route described below.

[0670] 4-chloro-6-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-2-phenylpyrimidine (4.33 g), dibenzo[b,d]thiophene-2-ylboronic acid (2.40 g), and (Amphos)2PdCl2 (0.28 g) were added to a flask. It was replaced with argon gas, 1,4-dioxane (67 mL), and 2 M of aqueous solution of sodium carbonate (12.5 mL) were added thereto, and then it was heated and stirred under reflux condition for 7 hours. After the reaction solution was cooled, water was added thereto, and the precipitated solid was collected by filtration. The crude product was purified by silica gel chromatography and recrystallization using xylene to obtain ET-17 as a white solid (4.13 g, 71% yield).

[0671] The mass spectrum thereof was analyzed as m / e=581 for a molecular weight of 580.74, and it was identified as an intended product.(Synthesis Example 18) Synthesis of ET-18

[0672] ET-18 was synthesized through the synthetic route described below.

[0673] 4-chloro-2,6-di(phenyl-2,3,4,5,6-d5)pyrimidine (3.50 g), 2-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.15 g), and (Amphos)2PdCl2 (0.22 g) were added to a flask. It was replaced with argon gas, 1,4-dioxane (126 mL), and 2 M of aqueous solution of sodium carbonate (15.8 mL) were added thereto, and then it was heated and stirred under reflux condition for 7 hours. After the reaction solution was cooled, dichloromethane was added thereto, and the resulting solution was filtered through silica gel. The crude product obtained by distilling off the solution was purified by silica gel chromatography, and washed with hexanes to obtain ET-18 as a white solid (5.03 g, 82% yield).

[0674] The mass spectrum thereof was analyzed as m / e=484 for a molecular weight of 483.66, and it was identified as an intended product.(Synthesis Example 19) Synthesis of ET-19

[0675] ET-19 was synthesized through the synthetic route described below.

[0676] 4-(4-bromo-1-naphthalenyl)-2-phenyl-6-(phenyl-2,3,4,5,6-d5)pyrimidine (3.00 g), 2-(7,7-dimethyl-7H-benzo[c]fluorene-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.64 g), and (Amphos)2PdCl2 (0.19 g) were added to a flask. It was replaced with argon gas, 1,4-dioxane (68 mL), and 2 M of aqueous solution of sodium carbonate (8.5 mL) were added thereto, and then it was heated and stirred at 74° C. for 7 hours. The reaction solution was cooled and filtered through silica gel. The crude product obtained by distilling off the solvent was purified by silica gel chromatography to obtain ET-19 as a white solid (2.59 g, 63% yield).

[0677] The mass spectrum thereof was analyzed as m / e=606 for a molecular weight of 605.79, and it was identified as an intended product.

[0678] Although only some exemplary embodiments and / or examples of this invention have been described in detail above, those skilled in the art will readily appreciate that many modifications are possible in the exemplary embodiments and / or examples without materially departing from the novel teachings and advantages of this invention. Accordingly, all such modifications are intended to be included within the scope of this invention.

[0679] The documents described in the specification and the specification of Japanese application(s) on the basis of which the present application claims Paris convention priority are incorporated herein by reference in its entirety.

Claims

1. A compound represented by the following formula (1):wherein in the formula (1),X1 and X2 are independently N or CH; any one of X1 and X2 is N;Ar1 and Ar2 are independentlya substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;L1 to L3 are independentlya single bond,a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, ora substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;n1 is integer 0 to 4; when n1 is 0, (L1)n1 is single bond; when a plurality of L1's is present, the plurality of L1's may be the same as or different from each other;n2 is integer 0 to 4; when n2 is 0, (L2)n2 is single bond; when a plurality of L2's is present, the plurality of L2's may be the same as or different from each other;n3 is integer 0 to 4; when n3 is 0, (L3)n3 is single bond; when a plurality of L3's is present, the plurality of L3's may be the same as or different from each other;R11 to R19 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R11 to R19 does not bond with each other;R21 and R22 form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form the substituted or unsubstituted, saturated or unsaturated ring;R21 and R22 which do not form the substituted or unsubstituted, saturated or unsaturated ring are independentlya hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, ora substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;the substituent R is selected from the group consisting ofa substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,—Si(R901)(R902)(R903),—O—(R904),—S—(R905),—N(R906)(R907),a halogen atom, a cyano group, a nitro group,a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, anda substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;R901 to R907 are independentlya hydrogen atom,a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, ora substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms;when two or more of each of R901 to R907 are present, the two or more of each of R901 to R907 may be the same as or different from each other; andwhen two or more substituents R are present, the two or more substituents R may be the same as or different from each other.

2. The compound according to claim 1, wherein the compound represented by formula (1) is a compound represented by the following formula (11):wherein in the formula (11),X1, X2, Ar1, Ar2, L1, L2, n1, n2, R11 to R19, R21, and R22 are the same as defined in the formula (1).3-4. (canceled)5. The compound according to claim 2, wherein R21 and R22 are methyl groups.

6. The compound according to claim 2, wherein X1 is N, and X2 is CH.

7. The compound according to claim 2, wherein the compound represented by the formula (11) is a compound represented by any one of the following formulas (111) to (113):wherein in the formula (111),L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);R111 to R120 is independently a hydrogen atom or a substituent R; a set of the adjacent two or more of Rill to R120 does not bond with each other;in the formula (112),L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);Y1 is N(R129), C(R130a)(R130b), O, or S;any one of R121 to R129 represents a bond with L2;R121 to R129 which do not represent a bond with L2 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R121 to R129 which do not represent a bond with L2 does not bond with each other;R130a and R130b form a substituted or unsubstituted, saturated or unsaturated ring by bonding with each other, or do not form the substituted or unsubstituted, saturated or unsaturated ring;R130a and R130b which do not form the substituted or unsubstituted, saturated or unsaturated ring are independently a hydrogen atom or a substituent R;R131 to R135 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R131 to R135 does not bond with each other;in the formula (113),L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);any one of R141 to R150 represents a bond with L2;R141 to R150 which do not represent a bond with L2 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R141 to R150 which do not represent a bond with L2 does not bond with each other;R151 to R155 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R151 to R155 does not bond with each other; andthe substituent R is the same as defined in the formula (1).

8. (canceled)9. The compound according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (21):wherein in the formula (21),X1, X2, Ar1, Ar2, L1, L2, n1, n2, R11 to R19, R21, and R22 are the same as defined in the formula (1);L21 isa substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, ora substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; andn21 is an integer 1 to 4; when a plurality of L21's is present, the plurality of L21's may be the same as or different from each other.10-11. (canceled)12. The compound according to claim 9, wherein R21 and R22 are methyl groups.

13. (canceled)14. The compound according to claim 9, wherein L21 isa substituted or unsubstituted phenylene group, ora substituted or unsubstituted naphthylene group.

15. The compound according to claim 9, wherein X1 is N, and X2 is CH.

16. The compound according to claim 9, wherein the compound represented by the formula (21) is a compound represented by the following formula (211) or (212):wherein in the formula (211),Ar1, Ar2, L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);R211 to R214 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R211 to R214 does not bond with each other;in the formula (212),Ar1, Ar2, L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);R221 to R226 are independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R221 to R226 does not bond with each other; andthe substituent R is the same as defined in the formula (1).

17. (canceled)18. The compound according to claim 9, wherein the compound represented by the formula (21) is a compound represented by the following formula (221) or (222):wherein in the formula (221),Ar1, Ar2, L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);R211 to R214 is independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R211 to R214 does not bond with each other;in the formula (222),Ar1, Ar2, L1, L2, n1, n2, and R11 to R19 are the same as defined in the formula (1);R221 to R226 is independently a hydrogen atom or a substituent R; a set of the adjacent two or more of R221 to R226 does not bond with each other; andthe substituent R is the same as defined in the formula (1).

19. (canceled)20. The compound according to claim 9, wherein Ar1 and Ar2 are independentlya substituted or unsubstituted phenyl group, ora substituted or unsubstituted naphthyl group.

21. The compound according to claim 1, wherein L1 and L2 are independentlya single bond,a substituted or unsubstituted phenylene group, ora substituted or unsubstituted naphthylene group.

22. The compound according to claim 1, wherein R11 to R19 are hydrogen atoms.23-25. (canceled)26. An organic electroluminescence device comprisinga cathode,an anode, andone or two or more organic layers arranged between the cathode and the anode,wherein at least one layer of the organic layers comprises the compound according to claim 1.

27. The organic electroluminescence device according to claim 26, which comprises the anode, an emitting layer, an electron-transporting region, and the cathode in this order, andthe electron-transporting region comprises the compound.

28. The organic electroluminescence device according to claim 27, wherein the electron-transporting region comprises a first layer and a second layer in this order from the emitting layer side, andthe first layer comprises the compound.

29. An electronic apparatus comprising the organic electroluminescence device according to claim 26.

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